Rhapontigenin

Rhapontigenin

Names
Preferred IUPAC name 5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)ethen-1-yl]benzene-1,3-diol
Other names Protigenin 3,3',5-trihydroxy-4'-methoxystilbene piceatannol 4'-methyl ether
Identifiers
CAS Number	500-65-2 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL113029
ChemSpider	4478875
PubChem CID	5320954
UNII	22BG4NNH6W Y
InChI InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+ Key: PHMHDRYYFAYWEG-NSCUHMNNSA-N
SMILES COc1ccc(cc1O)\C=C\c(cc2O)cc(O)c2
Properties
Chemical formula	C15H14O4
Molar mass	258.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Rhapontigenin is a stilbenoid. It can be isolated from Vitis coignetiae or from Gnetum cleistostachyum.

It shows an action on prostate cancer cells. It has been shown to inhibit the human cytochrome P450 1A1, an enzyme implicated in the biotransformation of a number of carcinogenic and immunotoxic compounds.

Injected in rats, rhapontigenin shows a rapid glucuronidation and a poor bioavailability.

See also

• Rhaponticin, its glucoside, found in rhubarb.
• Isorhapontigenin, a structural isomer.

External links

• Media related to Rhapontigenin at Wikimedia Commons